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2-Chloro-6-iodopyridin-3-ol

  • CAS No. 185220-68-2

  • Cat. No. CS-0036964
  • Purity≥95%
  • MDL No.MFCD10566651

*For research and further manufacturing use only, not for direct human use.

2-Chloro-6-iodopyridin-3-ol|CS-0036964

Structure of 185220-68-2

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General Information

  • CAS No. 185220-68-2
  • Cat. No. CS-0036964
  • Purity ≥95%
  • MDL No. MFCD10566651
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃ClINO
  • Molecular Weight None
  • Synonym(s) 2-chloro-6-iodo-3-pyridinol
  • SMILES C1=C(C(=NC(=C1)I)Cl)O

Description

2-Chloro-6-iodopyridin-3-ol features a halogenated pyridine core with complementary reactivity at the 2-chloro and 6-iodo positions, enabling selective cross-coupling transformations. The phenolic hydroxyl group enhances solubility and serves as a handle for derivatization. This bench-stable compound facilitates efficient access to complex heterocyclic architectures in medicinal chemistry and materials synthesis.

Application

2-Chloro-6-iodopyridin-3-ol serves as a versatile building block in the synthesis of functionalized pyridine derivatives. Its orthogonal halogenation pattern enables sequential cross-coupling reactions, with the chlorine facilitating Suzuki-Miyaura coupling and the iodine supporting Stille or Negishi protocols. The phenolic hydroxyl group provides a handle for derivatization or protection, enhancing synthetic flexibility. Bench-stable and amenable to standard purification methods, it supports efficient construction of complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Doebelin, Christelle; Wagner, Patrick; Bihel, Frederic; Humbert, Nicolas; Kenfack, Cyril Assongo; Mely, Yves; Bourguignon, Jean-Jacques; Schmitt, Martine Journal of Organic Chemistry, 2014 , vol. 79, # 3 p. 908 - 918
  • Route2

    References

    • US2004/53908 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   2.0452
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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